CA2372420A1 - Fluorescent retroreflective sheeting - Google Patents

Fluorescent retroreflective sheeting Download PDF

Info

Publication number
CA2372420A1
CA2372420A1 CA002372420A CA2372420A CA2372420A1 CA 2372420 A1 CA2372420 A1 CA 2372420A1 CA 002372420 A CA002372420 A CA 002372420A CA 2372420 A CA2372420 A CA 2372420A CA 2372420 A1 CA2372420 A1 CA 2372420A1
Authority
CA
Canada
Prior art keywords
layer
fluorescent
group
type
retroreflective sheeting
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002372420A
Other languages
French (fr)
Other versions
CA2372420C (en
Inventor
Ikuo Mimura
Akihiro Matsuda
Takashi Yoshioka
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nippon Carbide Industries Co Inc
Original Assignee
Nippon Carbide Kogyo Kabushiki Kaisha
Ikuo Mimura
Akihiro Matsuda
Takashi Yoshioka
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nippon Carbide Kogyo Kabushiki Kaisha, Ikuo Mimura, Akihiro Matsuda, Takashi Yoshioka filed Critical Nippon Carbide Kogyo Kabushiki Kaisha
Publication of CA2372420A1 publication Critical patent/CA2372420A1/en
Application granted granted Critical
Publication of CA2372420C publication Critical patent/CA2372420C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/12—Reflex reflectors
    • G02B5/126—Reflex reflectors including curved refracting surface
    • G02B5/128—Reflex reflectors including curved refracting surface transparent spheres being embedded in matrix
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/02—Coumarine dyes
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0003—Compounds of unspecified constitution defined by the chemical reaction for their preparation
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/02—Recovery or refining of essential oils from raw materials
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/12—Reflex reflectors
    • G02B5/122—Reflex reflectors cube corner, trihedral or triple reflector type
    • G02B5/124—Reflex reflectors cube corner, trihedral or triple reflector type plural reflecting elements forming part of a unitary plate or sheet
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31507—Of polycarbonate
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
    • Y10T428/31554—Next to second layer of polyamidoester
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31855—Of addition polymer from unsaturated monomers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Optics & Photonics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Physics & Mathematics (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Optical Elements Other Than Lenses (AREA)
  • Road Signs Or Road Markings (AREA)
  • Laminated Bodies (AREA)
  • Illuminated Signs And Luminous Advertising (AREA)

Abstract

A fluorescent retroreflective sheet of the confined-air type which comprises a surface-protective layer disposed on the side on which light is to strike, a binder layer connected to the surface-protective layer through a network bonding part, an air layer consisting of air confined by the network bonding part between the surface-protective layer and the binder layer, and a retroreflective element layer disposed between the surface-protective layer and the air layer (or between the binder layer and the air layer), wherein a t least one layer located on the light incidence side of the confined-air laye r contains at least one fluorescent dye selected from the group consisting of benzimidazole coumarin type fluorescent dyes represented by formula (1) and benzopyran type fluorescent dyes represented by formula (2). The sheet is excellent in appearance and long-lasting weatherability.

Claims (12)

1. Encapsulated type fluorescent retroreflective sheeting which comprises a surface-protective layer disposed on the side on which light is to strike, a binder layer connected to the surface-protective layer through network bonding parts, an air layer which is sealed-up by the network bonding parts between the surface-protective layer and the binder layer, and a retroreflective element layer disposed between the surface-protective layer and the air layer, or between the binder layer and the air layer, wherein at least one layer located on the light-incident side of sealed-up air layer contains at least one fluorescent dye selected from the group consisting of benzimidazole coumarin type-fluorescent dyes of formula (1) as follows:

wherein R1 and R2 each denote hydrogen atom, alkyl group, allyl group, cycloalkyl group, cyclohexylphenyl group or alkylphenyl group; and R3 and R4 each denote hydrogen atom, halogen atom, alkyl group or alkoxy group, and benzopyran type-fluorescent dyes of formula (2) as follows:

wherein Y1 and Y2 each denote hydrogen atom, cyano group, alkyl group, alkoxy group, allyl group, allyloxy group, carboalkoxy group, acetoxy-substituted alkyl group, cycloalkyl group or phenyl group; and Y3 and Y4 each denote hydrogen atom, halogen atom, alkoxy group, cyano group or nitro group.
2. Fluorescent retroreflective sheeting of claim 1 wherein the benzimidazole coumarin type-fluorescent dye of formula (1) is a yellow fluorescent dye of formula (1) wherein R1 and R2 each denote ethyl group and R3 and R4 each denote hydrogen atom.
3. Fluorescent retroreflective sheeting of claim 1 wherein the benzopyran type-fluorescent dye of formula (2) is a red fluorescent dye of formula (2) wherein Y1 and Y2 each denote allyl group and Y3 and Y4 each denote hydrogen atom.
4. Fluorescent retroreflective sheeting of claim 1 wherein at least one layer located on the light-incident side of sealed-up air layer contains said fluorescent dye in an amount of 0.01 to 0.5 PHR.
5. Fluorescent retroreflective sheeting of claim 1 wherein fluorescent dye-containing layer further contains a piperidine type hindered amine light stabilizer of tertiary amine structure which has a molecular weight of at least 600.
6. Fluorescent retroreflective sheeting of claim 5 wherein fluorescent dye-containing layer contains a piperidine type hindered amine light stabilizer in an amount 0 to 1 PHR.
7. Fluorescent retroreflective sheeting of claim 1 wherein retroreflective layer and/or surface-protective layer and/or fluorescent dye-containing layer include an ultraviolet absorber.
8. Fluorescent retroreflective sheeting of claim 7 wherein ultraviolet absorber is one of benzotriazole type or of benzophenone type.
9. Fluorescent retroreflective sheeting of claim 1 wherein retroreflective element layer comprises cube-corner type retroreflective elements.
10. Fluorescent retroreflective sheeting of claim 9 wherein cube-corner type retroreffective elements are triangular-pyramidal cube-corner retroreflective elements.
11. Fluorescent retroreflective sheeting of claim 1 wherein retroreffective element layer comprises micro glass beads type retroreflective elements.
12. Fluorescent retroreflective sheeting of claim 1 wherein resin which constitutes retroreffective element layer are polycarbonate resins, (meth)acrylic resins, vinyl chloride resins or urethane resins.
CA2372420A 2000-04-11 2001-02-22 Fluorescent retroreflective sheeting Expired - Fee Related CA2372420C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2000-109425 2000-04-11
JP2000109425A JP4028155B2 (en) 2000-04-11 2000-04-11 Fluorescent retroreflective sheet
PCT/JP2001/001294 WO2001077720A1 (en) 2000-04-11 2001-02-22 Fluorescent retroreflective sheet

Publications (2)

Publication Number Publication Date
CA2372420A1 true CA2372420A1 (en) 2001-10-18
CA2372420C CA2372420C (en) 2010-02-09

Family

ID=18622119

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2372420A Expired - Fee Related CA2372420C (en) 2000-04-11 2001-02-22 Fluorescent retroreflective sheeting

Country Status (8)

Country Link
US (1) US6911486B2 (en)
EP (2) EP2063295B1 (en)
JP (1) JP4028155B2 (en)
CN (1) CN1193241C (en)
CA (1) CA2372420C (en)
ES (1) ES2396660T3 (en)
HK (1) HK1046732B (en)
WO (1) WO2001077720A1 (en)

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Also Published As

Publication number Publication date
EP1273933A4 (en) 2003-09-03
JP4028155B2 (en) 2007-12-26
EP2063295A1 (en) 2009-05-27
CN1193241C (en) 2005-03-16
CN1366619A (en) 2002-08-28
WO2001077720A1 (en) 2001-10-18
US20030100637A1 (en) 2003-05-29
EP2063295B1 (en) 2012-04-18
HK1046732A1 (en) 2003-01-24
US6911486B2 (en) 2005-06-28
ES2396660T3 (en) 2013-02-25
HK1046732B (en) 2005-11-04
EP1273933A1 (en) 2003-01-08
CA2372420C (en) 2010-02-09
JP2001296413A (en) 2001-10-26

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